Starting a charity event 101

I work for a non-profit that serves youths throughout the county. We're always trying to raise money to continue and expand (ie serve more children).

I want to spearhead a project--one that i believe in (check), one that i'll enjoy (check), and one that will help my company (check) and my employment at that company (check).

I want to set up a ride that starts in the town we're located in and rolls through the major cities that we serve. This would allow a few different routes (millages) so that we could attract the avid cyclists and the families in the area.

The goal would be to gain exposure and hopefully earn a few bucks and (more importantly) some new volunteers/childern.

I talked to our marketing person about this, she didn't take me seriously saying (Hey, if you figure it out, i'll be there to help). I'm taking that statement seriously, and i'd like to have something set up by next summer.

What is involved in setting up a ride like this?
What approvals do you need from the various cities/townships?
What costs must you expect?
What legalities are involved (waivers, etc)?

Your best bet is probably to talk to someone at the National MS Society. They have been doing the MS150 (now Bike MS) rides for over 20 years, and have all of the details sorted and down to a science. Even then, things are still evolving.

For example, for their SAG drivers, the National Office has decreed that all drivers must have a background check peformed (I am assuming some perceived liability issue) before they can drive one of the vans.

Your best bet is probably to talk to someone at the National MS Society. They have been doing the MS150 (now Bike MS) rides for over 20 years, and have all of the details sorted and down to a science. Even then, things are still evolving.

For example, for their SAG drivers, the National Office has decreed that all drivers must have a background check peformed (I am assuming some perceived liability issue) before they can drive one of the vans.

Hmm, i'll look into that.

I was also thinking today that i should go to the biggest LBS in the area and chat with them about it.

You may want to get in contact with several ride organizers in your region and see what it takes to promote them.

I know the Tour de Cure has my eMail box hit with email all year long, and some hard copy in my PO box at least once per month. They also advertise, have corporate sponsors, and have a huge national push, and hope to get like 500 riders for the eastern half of Pennsylvania this year to ride on one of the most beautiful rides in the region.

It seems like it should be get a few cities to sign off on your plan, get insurance, get a few volunteers, put out a few flyers and then enjoy the ride, but I suspect you are signing up for a lot of work...